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Pulegone information


Pulegone[1]
Names
Preferred IUPAC name
(5R)-5-Methyl-2-(propan-2-ylidene)cyclohexan-1-one
Other names
p-Menth-4(8)-en-3-one;
δ-4(8)-p-Menthen-3-one;
(R)-2-Isopropylidene-5-methylcyclohexanone;
(R)-p-Menth-4(8)-en-3-one;
(R)-(+)-Pulegone
Identifiers
CAS Number
  • 89-82-7 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:35596 checkY
ChemSpider
  • 390923 checkY
ECHA InfoCard 100.001.767 Edit this at Wikidata
PubChem CID
  • 442495
UNII
  • 4LF2673R3G checkY
CompTox Dashboard (EPA)
  • DTXSID2025975 Edit this at Wikidata
InChI
  • InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1 checkY
    Key: NZGWDASTMWDZIW-MRVPVSSYSA-N checkY
  • InChI=1/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3/t8-/m1/s1
    Key: NZGWDASTMWDZIW-MRVPVSSYBS
SMILES
  • O=C1/C(=C(/C)C)CC[C@@H](C)C1
Properties
Chemical formula
C10H16O
Molar mass 152.237 g·mol−1
Appearance Colorless oil
Density 0.9346 g/cm3
Boiling point 224 °C (435 °F; 497 K)
Solubility in water
Insoluble
Solubility in Ethanol
Ether
Chloroform
Miscible
Hazards
Safety data sheet (SDS) MSDS[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita, and pennyroyal.[3][4] It is classified as a monoterpene.

Pulegone is a clear colorless oily liquid and has a pleasant odor similar to pennyroyal, peppermint and camphor. It is used in flavoring agents, in perfumery, and in aromatherapy.

  1. ^ Merck Index, 11th Edition, 7955.
  2. ^ Universiti Malaysia Pahang. "Safety data sheet" (PDF). Retrieved 8 June 2009.[permanent dead link]
  3. ^ Grundschober, F. (1979). "Literature review of pulegone". Perfum. Flavorist. 4: 15–17.
  4. ^ Sullivan, J.B., Rumack, B.H., Thomas, H., Peterson, R.G. & Brysch, P. (1979). "Pennyroyal oil poisoning and hepatotoxicity". J. Am. Med. Assoc. 242 (26): 2873–2874. doi:10.1001/jama.1979.03300260043027. PMID 513258.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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Pulegone

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Pulegone is a naturally occurring organic compound obtained from the essential oils of a variety of plants such as Nepeta cataria (catnip), Mentha piperita...

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Mentha pulegium

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pennyroyal is pulegone. Pulegone is a ketone and on the cellular level, ketones can act as enzyme inhibitors. The carbonyl center of the pulegone structure...

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Menthol

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isomerase (iPI) then isomerizes the remaining double bond to form (+)-pulegone. (+)-Pulegone reductase (PR) reduces this double bond using NADPH to form (−)-menthone...

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Peppermint

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contains small amounts of many additional compounds, including limonene, pulegone, caryophyllene, and pinene. Peppermint contains terpenoids and flavonoids...

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Menthofuran

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rearrangement. Menthofuran is a metabolite of pulegone. Both in vitro and in vivo studies have found the pulegone metabolite menthofuran to be an inhibitor...

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List of poisonous plants

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Catalfamo, M; Cautela, D; Servillo, L; Castaldo, D (2005). "Analysis of pulegone and its enanthiomeric distribution in mint-flavoured food products". Food...

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Minthostachys mollis

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from Quechua. The principal components of essential oil are as follows: pulegone menthone menthol (−)-β-pinene (−)-α-pinene limonene isomenthone piperic...

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C10H16O

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4-Decadienal Fenchone (S)-Ipsdienol Myrtenol Perillyl alcohol Piperitone Pulegone Thujone Verbenol This set index page lists chemical structure articles...

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Monoterpene

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According to a review, several studies showed "that some monoterpenes (e.g., pulegone, menthofuran, camphor, and limonene) and sesquiterpenes (e.g., zederone...

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Glechoma hederacea

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hederacea contains bioactive volatile oils, including terpenoids and pulegone; these are responsible for the characteristic "minty" odor and taste of...

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Mentha longifolia

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Mentha species, is known to have important medicinal properties. Menthol Pulegone BSBI List 2007 (xls). Botanical Society of Britain and Ireland. Archived...

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Mentha

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are menthol (the main aroma of peppermint and Japanese peppermint) and pulegone (in pennyroyal and Corsican mint). The compound primarily responsible for...

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Pyridinium chlorochromate

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cyclization, is illustrated by the conversion of (−)-citronellol to (−)-pulegone. PCC also effects allylic oxidations, for example, in conversion of dihydrofurans...

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IARC group 2B

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Progestogen-only contraceptives β-Propiolactone Propylene oxide Propylthiouracil Pulegone Pyridine Quinoline Radiofrequency electromagnetic fields Refractory ceramic...

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Phycocyanin

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treated against heptatoxins such as Carbon tetrachloride (CCl4) or R-(+)-pulegone. C-PC protects the liver by the means of the Cytochrome-P450 system. It...

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Mentha canadensis

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essential oil and menthol production. It also contains a significant amount of pulegone. The leaves have a distinct peppermint smell when pinched or crushed as...

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Hedeoma pulegioides

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perspiration and as an emmenagogue." Upon ingestion, one of its components, pulegone, metabolizes into hepatotoxic metabolites that depending on dosage can...

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Construction of electronic cigarettes

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pyrazines. Flavor components include eucalyptol, camphor, methyl salicylate, pulegone, ethyl salicylate, cinnamaldehyde, eugenol, diphenyl ether, coumarin, diacetyl...

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Thiol

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Kume, Fumitaka; Frye, Stephen V. (1993). "Chiral 1,3-oxathiane from (+)-Pulegone: Hexahydro-4,4,7-trimethyl-4H-1,3-benzoxathiin". Organic Syntheses; Collected...

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Artemisinin

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early days until today, including total synthesis routes from (R)-(+)-pulegone, isomenthene, and even 2-cyclohexen-1-one, as well as routes better described...

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Nicholas Culpeper

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helping expel gas. (The active constituent of pennyroyal is now known to be pulegone.) Savory, for helping expel gas, and mixed with peas and beans for this...

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Mentha cervina

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pulegium or pennyroyal. The plants were associated due to their shared high pulegone content, which gives them both a distinctive, strong aroma. A sprawling...

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Olivetol

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citation needed] One such method is a condensation reaction of olivetol and pulegone.[citation needed] In PiHKAL, Alexander Shulgin reports a cruder method...

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California Proposition 65 list of chemicals

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mono-t-butyl ether 57018-52-7 Propylene oxide 75-56-9 Propylthiouracil 51-52-5 Pulegone 89-82-7 Pymetrozine 123312-89-0 Pyridine 110-86-1 Pyrimethamine 58-14-0...

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Schizonepeta

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contains the following constituents: four monoterpenes: (−)-menthone, (+)-pulegone, (−)-limonene and (+)-menthofuran as the main bio-active and toxic constituents...

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